I manually update all of my option positions in Quicken and only let it update my stock position automatically.

It will update option positions automatically "if" you let Quicken have access/update from your trading account. I did not like the possible security problems that could possibly occur from that, nor did I like the "value" it assigned to a position.

I don't remember if automatically letting Quicken update the position gave me a last price (which could be several days old) or an average of the bid/ask position (not as bad, but not accurate in my opinion).

Manually, if I am long a position, I enter the bid price (and the high, low and volume for the day); and if I am short, I enter the asking price (and the high, low and volume). In my opinion, these are the TRUE prices for my options, as they represent the current price that I can exit the positions I am holding.